A complete study has been made of the reaction of tris(methylthio)methyllithium with aromatic, heteroaromatic, and aliphatic esters. It is a one-pot reaction that despite its complexity, and depending on the reagent ratios, the reaction conditions, and the possible use of additional reagents (N-(methylthio)phthalimide or BuLi), can supply easily, in excellent and reproducible yields, the trimethyl a-keto trithioorthoesters 3 or, alternatively, the dimethyl a-keto dithioacetals 4. The reaction mechanism has been elucidated.

Synthesis of trimethyl a-Keto Trithioorthoesters and Dimethyl a-Keto dithioacetals by reaction of esters with tris(methylthio)methyllithium

BARBERO, Margherita;CADAMURO, Silvano;DEGANI, Jacopo;DUGHERA, Stefano;FOCHI, Rita
1995-01-01

Abstract

A complete study has been made of the reaction of tris(methylthio)methyllithium with aromatic, heteroaromatic, and aliphatic esters. It is a one-pot reaction that despite its complexity, and depending on the reagent ratios, the reaction conditions, and the possible use of additional reagents (N-(methylthio)phthalimide or BuLi), can supply easily, in excellent and reproducible yields, the trimethyl a-keto trithioorthoesters 3 or, alternatively, the dimethyl a-keto dithioacetals 4. The reaction mechanism has been elucidated.
60
6017
6024
tris(methylthio)methyllithium; esters; reaction mechanism.
BARBERO M; CADAMURO S; DEGANI I; S. DUGHERA; FOCHI R
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/4437
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